Hydrochloric Acid → Methyl naphthalen-1-ylglycinate

Participants

Reaction Steps

The N-3,5-dinitrobenzoyl-(R) or (S)-(α-naphthyl)-glycine of formula (III) may be prepared in a common method. For example, commercially available α-naphthylacetonitrile is treated with hydrogen chloride in methanol to thereby give methyl(α-naphthyl)acetoimidate. Then the resulting product is treated with sodium hypochlorite and sodium methylate to give (α-naphthyl)glycine methyl ester. Then this product is treated with 3,5-dinitrobenzoyl chloride. The N-3,5-dinitrobenzoyl-(RS)-(α-naphthyl)glycine methyl ester thus obtained is hydrolyzed to thereby give N-3,5-dinitrobenzoyl-(RS)-(α-naphthyl)glycine which is then optically resolved. Thus the aimed compound can be obtained.

Provenance & Evidence